[Remote] Principal Technical Writer

Note: The job is a remote job and is open to candidates in USA. Toast creates technology to help restaurants and local businesses succeed in a digital world. As a Principal Technical Writer, you will design and deliver product information for enterprise customers, focusing on enabling self-implementation and self-support through documentation and AI-driven content generation. Responsibilities • Remove obstacles to self-implementation and self-support for complex customer businesses by designing and writing cross-cutting enablement documentation. Write for enterprise customer technical leadership and support teams, producing implementation guides, architecture overviews, integration patterns, and best practices. Use research, interviews, and collaboration with Toast customer-facing teams to understand business objectives, pain points, and implementation barriers • Build and implement AI documentation generation infrastructure, establish evaluation frameworks to verify content quality, and advocate for AI tool adoption to accelerate discovery and shape how we document at scale • Collaborate as a strategic leader in developing documentation practice, focused on business enablement writing and AI-driven product documentation infrastructure • Cover multiple product functionality areas as a domain expert, using AI tooling for routine documentation updates and focusing your writing on strategic enablement content. For example, topic areas might include menu configuration, multi-location management, and enterprise configuration controls • Partner with peer product development leaders to incorporate documentation requirements into product development planning from the start • Test complex technical features, write and validate code examples, and advocate for enterprise developer experience • Measure and communicate documentation impact on enterprise customer implementation time, support ticket volume, and adoption metrics • Mentor technical writers in adopting AI tools, balancing strategic thinking with execution, and establishing documentation quality standards Skills • 8+ years of technical writing experience for enterprise products, with demonstrated ownership of major documentation domains or platforms • Deep expertise in developer documentation: REST APIs, OpenAPI/Swagger, authentication protocols, integration patterns, webhooks, data models • Experience writing for technical decision-makers (engineering leaders, CTOs, enterprise architects) and complex implementation scenarios • Proven ability to design cross-cutting documentation strategies that solve problems affecting multiple audiences (developers, integrators, support teams, customers), with effective management of ambiguity in problem definition • Hands-on experience with AI documentation tools or demonstrated ability to evaluate AI-generated content for accuracy, completeness, and usefulness • Strong technical fluency: comfortable testing APIs, writing code examples, understanding system architecture, and partnering with engineering teams as a technical peer • Demonstrated expertise in information architecture for complex product ecosystems—designing maintainable documentation structures • Strong systems thinking: ability to balance short-term documentation delivery with long-term architectural integrity and scalability • Excellent stakeholder management and ability to influence product development teams to include product information and communication as part of the definition of done • Track record of influencing product development culture to treat documentation as a product quality requirement • Experience mentoring technical writers or contributing to documentation practice development across teams • Familiarity with documentation-as-code workflows, CI/CD for documentation, and docs infrastructure (static site generators, version control, automated testing) • Experience with docs analytics and measuring documentation effectiveness (search analytics, page performance, user feedback) • Experience in fast-growing SaaS companies navigating enterprise market expansion • Experience with restaurant technology, POS systems, hospitality software, or similar physical-world operational technology • Experience with change management, enterprise customer onboarding, or field enablement Benefits • Cash compensation (overtime, bonus/commissions if eligible) • Equity • Benefits • Flexibility to meet Toasters’ changing needs • Reasonable accommodations for persons with disabilities to enable them to access the hiring process Company Overview • Toast is a point-of-sale and restaurant management platform designed for businesses in the food service and hospitality industry. It was founded in 2011, and is headquartered in Bo